Methyl iodide → 2-Chloro-9-cyclopentyl-7,7-difluoro-5-methyl-8,9-dihydro-5H-pyrimido[4,5-B][1,4]diazepin-6(7H)-one

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Reaction Steps

2-Chloro-9-cyclopentyl-7,7-difluoro-8,9-dihydro-5H-pyrimido[5,4-b][1,4]diazepin-6(7H)-one (2.4 g, 7.95 mmol) was dissolved in DMA (20 mL) and cooled in an ice bath. Sodium hydride (348 mg of 65% in mineral oil, 8.75 mmol) was added slowly and left to stir for 10 minutes. Methyl iodide (0.546 mL, 8.75 mmol) was then added and then after 10 minutes the solution removed from the bath. After 30 minutes the reaction was deemed complete by LCMS, poured into ice water (300 mL), the solution acidified with 1N HCl, the product filtered off as a yellow solid (2.36 g, 94% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.38-2.00 (m, 8 H) 3.34 (s, 3 H) 4.15 (t, J=13.26 Hz, 2 H) 4.80 (q, 1 H) 8.35 (s, 1 H). [M+H] calc'd for C13H15ClF2N4O, 317; found 317.

Provenance & Evidence